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Formamide-Based Prebiotic Synthesis of Nucleobases: A Kinetically Accessible Reaction Route

Basic information
Original title:Formamide-Based Prebiotic Synthesis of Nucleobases: A Kinetically Accessible Reaction Route
Authors:Judit Šponerová, Arnošt Mládek, Jiří Šponer, Miguel Fuentes-Cabrera
Further information
Citation:ŠPONEROVÁ, Judit, Arnošt MLÁDEK, Jiří ŠPONER and Miguel FUENTES-CABRERA. Formamide-Based Prebiotic Synthesis of Nucleobases: A Kinetically Accessible Reaction Route. The Journal of Physical Chemistry A, Washington: American Chemical Society, 2012, vol. 116, No 1, p. 720-726. ISSN 1089-5639. doi:10.1021/jp209886b.Export BibTeX
@article{969344,
author = {Šponerová, Judit and Mládek, Arnošt and Šponer, Jiří and FuentesandCabrera, Miguel},
article_location = {Washington},
article_number = {1},
doi = {http://dx.doi.org/10.1021/jp209886b},
keywords = {CHEMICAL EVOLUTION; HYDROGEN-CYANIDE; PRIMITIVE EARTH; RING FORMATION; ADENINE; ORIGIN; PURINE; MECHANISM; ENERGIES; WATER},
language = {eng},
issn = {1089-5639},
journal = {The Journal of Physical Chemistry A},
title = {Formamide-Based Prebiotic Synthesis of Nucleobases: A Kinetically Accessible Reaction Route},
url = {http://pubs.acs.org/doi/full/10.1021/jp209886b},
volume = {116},
year = {2012}
}
Original language:English
Field:Physical chemistry and theoretical chemistry
WWW:link to a new windowhttp://pubs.acs.org/doi/full/10.1021/jp209886b
Type:Article in Periodical
Keywords:CHEMICAL EVOLUTION; HYDROGEN-CYANIDE; PRIMITIVE EARTH; RING FORMATION; ADENINE; ORIGIN; PURINE; MECHANISM; ENERGIES; WATER

Synthesis of nucleobases in nonaqueous environments is an alternative way for the emergence of terrestrial life, which could solve the fundamental problem connected to the hydrolytic instability of nucleic acid components in an aqueous environment. In this contribution, we present a plausible reaction route for the prebiotic synthesis of nucleobases in formamide, which does not require participation of the formamide trimer and aminoimidazole-carbonitrile intermediates. The computed activation energy of the proposed pathway is noticeably higher than that of the HCN-based synthetic route, but it is still feasible under the experimental conditions of the Saladino synthesis. We show that, albeit both the pyrimidine and purine ring formation utilizes the undissociated form of formamide, the dehydration product of formamide, HCN, may also play a key role in the mechanism. The rate determining step of the entire reaction path is the cyclization of the diaza-pentanimine precursor. The subsequent formation of the imidazole ring proceeds with a moderate activation energy. Our calculations thus demonstrate that the experimentally suggested reaction path without the involvement of aminoimidazole-carbonitrile intermediates is also a viable alternative for the nonaqueous synthesis of nucleobases.

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